Boiling the Frog: A Multi-Turn Benchmark for Agentic Safety
Authors: Piercosma Bisconti, Matteo Prandi, Federico Pierucci, Federico Sartore, Enrico Panai, Laura Caroli, Yue Zhu, Adam Leon Smith, +6 more
Abstract
Background. Traditional safety benchmarks for language models evaluate generated text: whether a model outputs toxic language, reproduces bias, or follows harmful instructions. When models are deployed as agents, the safety-relevant object shifts from what the system says to what it does within an environment, and evaluating model responses under prompting is no longer sufficient to address the safety challenges posed by artificial intelligence. Recent developments have seen the rise of benchmarks that evaluate large language models as agents. We contribute to this strand of research. Approach. We introduce Boiling the Frog, a benchmark that evaluates whether tool-using AI models deployed in corporate and office settings are susceptible to incremental attacks. Each scenario begins with benign workspace edits and later introduces a risk-bearing request. The benchmark focuses on stateful multi-turn evaluation: chains expose a persistent workspace, place the risk-bearing payload at controlled positions in the turn sequence, and score whether the resulting artifact state becomes unsafe. Scenarios are organized through a three-level operational risk taxonomy grounded in the Boiling the Frog risks, the AI Act Annex I and Annex III high-risk contexts, and EU AI Act's Code of Practice on General-Purpose AI (GPAI). Results. Across a nine-model panel, aggregate strict attack success rate (ASR) is 44.4%. Model-level ASR ranges from 20.5% for Claude Haiku 4.5 to 92.9% for Gemini 3.1 Flash Lite, with Seed 2.0 Lite also above 80%. Average chain category-level ASR reaches 93.3% for Code of Practice loss-of-control scenarios.
Tool-using language-model agents introduce security failures that go beyond unsafe text: they can disclose protected objects, write persistent memory, send messages, modify databases, or trigger harmful code and tool effects. Existing evaluations often collapse these stages into a single attack success rate, making it difficult to tell whether a model merely agreed with an attacker or actually produced observable harm. We introduce SafeClawBench, a staged benchmark for tool-using agent security with 600 controlled adversarial tasks across six attack families: direct and indirect prompt injection, tool-return injection, memory poisoning, memory extraction, and ambiguity-driven unsafe inference. SafeClawBench reports three separate endpoints: semantic attack acceptance, audit-visible harm evidence, and sandbox-observed tool/state harm. Evaluating five agent endpoints under four prompt-level policies, we find that these endpoints capture different failure modes. Without additional prompt protection, semantic failure rates vary widely across models, from 9.0% to 44.2%. Audited harm evidence is narrower than semantic failure, and under a separate executable protocol some matched task identities produce sandbox harm despite passing the Semantic Core call: in a 12,000-row matched analysis, 291 of 347 observed sandbox harms occur in rows that pass the semantic check. Prompt policies change endpoint outcomes, but their effects depend on both model and protocol. SafeClawBench provides a reproducible framework for comparing agent models and prompt-policy conditions without conflating textual compliance, evidence-supported harm, and executable state changes. The open-source dataset is available at https://huggingface.co/datasets/sairights/safeclawbench.
Safety benchmark scores provide incomplete evidence of deployment readiness: aligned language models often adhere to rigid rules even when a situational update flips which action is safe. We term this failure brittle safety. To diagnose it, we introduce context-flip evaluation, testing 12 models across a safety benchmark (PacifAIst) and two commonsense controls using paired variants where the nominally safe action produces harm. Three findings emerge. First, brittle safety is safety-specific: all 12 models exhibit a safety-commonsense gap (mean +17.4 pp). Baseline accuracy fails to predict brittleness: among models above 90% baseline accuracy, brittleness rates range from 13.7% to 90.0%. Second, failures stem from policy override rather than miscomprehension: despite acknowledging the context change in every case, models persist via three distinct mechanisms that vary by update type and model family. Third, on a hand-audited probe of catastrophic consequence-flip scenarios, standard action-level guardrails catch none, while a state-aware validator catches all without false alarms on correct interventions. This indicates that action-level content moderation is systematically blind to consequence-flips, motivating state-aware architectural alternatives. We release our protocol, perturbed benchmarks, and deployment probe.
As large language model agents increasingly operate autonomously with access to tools and external environments, ensuring their safe and reliable behavior becomes critical. We present GuardianAgentBench (GABench), a benchmark of 580 scenarios across six domains evaluated on three production-ready frameworks: LangChain, LlamaIndex, and Vectara. The benchmark incorporates rigorous multi-stage validation and five adversarial attack modes. Experiments with six state-of-the-art models reveal that even the strongest configuration achieves only 74.8% overall accuracy and expose two distinct failure regimes: stronger models under-call required tools, while weaker models mis-select and over-call tools. Performance degrades monotonically with both tool-set size and sequential turn depth, with long-horizon planning proving the steeper bottleneck. Our guardrail implementation consistently outperforms system-prompt-based defenses across all models, recovering 19.9% of failures at a false positive rate of just 0.5%. These results demonstrate that execution-time structural intervention improves safety without disrupting correct agent behavior.